After a few years in the workforce, you rack up a whole bunch of stories about your co-workers, your customers, and the one person who controls you all: your boss. 

A boss has the power to make a lot of people’s lives a living hell, and while there are many wonderful and compassionate managers out there, those make for pretty boring stories. 

So, let’s read about the awful ones!

Podcaster Chris Caesar asked his followers for their juiciest, most terrible and most insane boss stories. He was especially interested in ones that were so bananas you wouldn’t even believe them if you hadn’t witnessed the event. 

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There were a lot of stories that did seem too crazy to be true, but the thing is, we’ve all encountered some version of even the most horrible of bosses. 

Maybe the rest of our experiences aren’t as extreme, but a lot of these are actually very relatable.

Take this boss, who clearly values mind-bending sci-fi plots over any version of morality or how things actually scientifically work.

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Or this boss with a penchant for violence, second amendment rights, and a really short fuse:

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Then there’s the kind of supervisor who will make everyone dress according to their personal dress code, not taking into account the fact that people come in different shapes and sizes, or that not everyone is keen on sporting a jersey for a team the boss is a fan of.

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Or the boss who has no concept of personal boundaries or HR, for that matter, and acts like he’s still in middle school.

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Ah yes, the classic “I don’t believe in sick days” kind of boss for whom no ailment excuses an absence. Who cares about your 110 fever when you have a shift to work?!

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There’s the kind of boss experience that is only insane because of the intimate details you know about their personal life. TMI!

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How about the kind of boss who can’t be trusted around the merchandise you guys sell? Because we’ve got one of those too.

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The boss who seemed like he had good intentions, but ultimately just wanted some innocent employees to take the fall for his actions.

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Check out this guy who thinks that anything in his office belongs to him, and has zero shame about it.

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It probably came as a surprise to literally no one that the legal system ended up having to get involved here.

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This boss tried so hard to be understanding and empathetic with her employee—but then pretty much completely missed the mark.

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We’ve all met some of these bosses, and in some unfortunate cases, one manager has displayed several of these unattractive qualities. It’s messed up, but at least all of these people escaped with a great story.

And this has made me appreciate my boss even more. If you’re reading this, thanks for letting me work from home!


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